Fiddler on the Roof and Whether I Like My Job

Often, when I get frustrated or sad at work, I find my thoughts turning to the question of why I’m even running a company in the first place.

When we first started Castle, back in 2014, people would ask me all the time whether I “liked” being a startup founder. And every time it felt like being asked if I liked a roller coaster that I had just gotten on. It wasn’t that I didn’t like the job; it was just that it was all moving too fast for the question to even apply. I just got on this ride, I’d think. You can ask me if I liked it once I get to the end.

Now it’s been years and the roller coaster metaphor has become less and less apt every day. My life moves just as fast, maybe even faster, but that’s the new normal; like the apocryphal frog in boiling water, I’m so used to the pace that I hardly notice it anymore. And I’ve grown so far beyond the 24-year-old who decided to start this company that he might as well be a stranger. I barely remember him, but I’m still living with the consequences of his decisions every day.

Every attempt at writing down my reasons for doing this ends in a list of clichés that I’m not sure I even believe: wanting to be my own boss, to have an impact on the world, to build a community, to challenge myself. I’m more sure of the motives that don’t reflect as well on me: wanting to seem important, to have my ego stroked, to prove that I can try on the costume of a successful person without everybody noticing that I’m wearing someone else’s clothes.

Or maybe it’s just that I’ve always been the type to optimize my life for the highs, no matter how deep the corresponding lows. The lows that come with this job are brutal: weeks if not months where I’m convinced that I’m an idiot, a fraud, running the company into the ground, letting everyone around me down, squandering the millions of dollars I conned people into trusting me with in the first place.

But the highs — the highs are like nothing else. And not just the obvious milestones like closing a fundraising round but the subtle ones, the quiet moments of grace that I could never put in an investor pitch or a TechCrunch article: realizing that a problem has been discovered and solved without my even noticing. Or overhearing someone use one of our core values to describe something that’s happening in their life. Or the stupid inside joke that spiraled uncontrollably until it became a set of matching tattoos that could easily be the most lasting thing our company creates.

Or the time someone fought back tears while telling me how much working here has meant to them.

I’m still not sure if I like this job. “Like” seems like such a simple word to apply to the maelstrom of emotions that battle when I think about the thing I’ve chosen to devote this chapter of my life to. How crude to be forced to compress so much into such a tiny, insignificant term.

But I know that I want to be here. That I find myself compelled to do this, to keep doing it, for reasons I can’t fully explain, let alone understand myself. That I’ll give this everything I’ve got — because I believe in it, yes, but also because in the end it feels better to give a thing your all, no matter what that thing is.

When I was writing the first draft of what became this essay, I kept finding myself thinking about the song “Do You Love Me?,” from the musical Fiddler on the Roof. I’m not sure why this one song has stuck with me so much, since Fiddler is far from my favorite musical and “Do You Love Me” far from my favorite of the show’s songs.

It comes near the end of the play, after the protagonists — a husband and wife in one of Imperial Russia’s Jewish settlements — have watched their daughters break with their community’s tradition of arranged marriages, spurning their designated suitors for men they have chosen on their own. The parents, watching from the sidelines as this cultural shift sweeps through their family, find themselves reassessing their own arranged marriage. And they’re faced, for the first time, with the question of whether or not they love each other.

The song is spare and simple, with only a few short verses and none of the orchestral swelling one typically associates with musicals. Its lyrics frame love not as a feeling but instead as the slow accumulation of a series of choices — to live with each other, to learn from each other, to care for each other — that the pair has made over the years. What else could those choices add up to, they conclude, but love?

And I guess that’s how it is with me, too. I struggle to imagine my life without this job. Most days I care about it, and the people in it, more than almost anything else — and even on the days when I don’t, I act like I do anyways. I pour so much of myself into it, squeeze so much out of myself for it, that the boundaries between us dissolve into a blurry haze.

And so if all of that doesn’t mean I love my job, what possibly could?